L-Alanine → HCID 54751151, compound

HRID 1511964Notes

Reaction equation

HRID 1511964 reaction equation
CO[C:3]([C:5]1[C:17](=[O:18])[N:16]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[N:15]2[C:7](=[CH:8][C:9]3[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]=1[OH:27])=[O:4].[NH2:28][C@H:29]([C:31]([OH:33])=[O:32])[CH3:30].C[O-].[Na+]>COCCO>[F:26][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:16]2[N:15]3[C:7](=[CH:8][C:9]4[C:14]3=[CH:13][CH:12]=[CH:11][CH:10]=4)[C:6]([OH:27])=[C:5]([C:3]([NH:28][C@@H:29]([CH3:30])[C:31]([OH:33])=[O:32])=[O:4])[C:17]2=[O:18])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 5950L-AlanineHCID 10942334Sodium MethoxideHCID 68761498HCID 68761498, compound

Product 1

HCID 54751151HCID 54751151, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of 4-(4-fluoro-benzyl)-1-hydroxy-3-oxo-3,4-dihydro-4,4a-diaza-fluorene-2-carboxylic acid methyl ester (110 mg), L-alanine (268 mg), NaOMe (146 mg) in 2-methoxyethanol (10 mL) was refluxed for 6 h; subsequently, the reaction was cooled and solvent was removed by rotovaping; the residue was dissolved in water and then acidified with 2 M HCl solution; the precipitates were collected via filtration, washed with water, dried, and then purified with column (eluent: DCM/EtOAc, 10/1 (v/v), with 0.5% acetic acid) to give the desired product (78 mg). ESI (m/z): 424 (M+H)+.

Workup

  1. temperaturewas refluxed for 6 h
  2. temperaturesubsequently, the reaction was cooled
  3. customsolvent was removed
  4. dissolutionthe residue was dissolved in water
  5. filtrationthe precipitates were collected via filtration
  6. washwashed with water
  7. customdried
  8. custompurified with column (eluent: DCM/EtOAc, 10/1 (v/v), with 0.5% acetic acid)

Sources & evidence

ORD record
ord-18ca9d528dd4442e8b77637dbca7b7a7
Source dataset
uspto-grants-2012_07
Patent number
US08217043B2

Reaction notes

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